Cesium carbonate → 4-{[5-(3-Chlorophenyl)-4-(3-methoxyphenyl)furan-2-yl]carbonyl}piperazin-2-one

HRID 2190144Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:14]([N:16]2[CH2:21][CH2:20][NH:19][C:18](=[O:22])[CH2:17]2)=[O:15])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:13][C:9]1[CH:8]=[C:7]([C:6]2[O:5][C:4]([C:14]([N:16]3[CH2:21][CH2:20][NH:19][C:18](=[O:22])[CH2:17]3)=[O:15])=[CH:3][C:2]=2[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([O:24][CH3:23])[CH:30]=2)[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

50.0 mg (0.13 mmol) of the compound from Example 27A are provided in 5 ml of 1,2-dimethoxyethane/water (4:1), 19.8 mg (0.13 mmol) of 3-methoxyphenylboronic acid, 4.4 mg (0.009 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane, 0.9 mg (0.004 mmol) of palladium(II) acetate and 127 mg (0.39 mmol) of cesium carbonate are added and the mixture is heated in a closed glass vessel under microwave irradiation at 120° C. for one hour. The reaction mixture is subsequently purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 30.0 mg (56% of theory) of the title compound are obtained.

Workup

customThe reaction mixture is subsequently purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-e7654c3275064705a52d5cdcd75c4924
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324268B2

Reaction notes

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